I hate Jim Lee's Joker but i really do not get what you mean with transgender/crossdresser wannabe. That, along with sadomasochism have always been arround the Joker. It has been well-established that he reinvents himself, he is not only 1 person but multiple with the same basic characteristics, of a clown. Clowns originate from the Ancient Greeks and the rites of Dionysus where sexuality and transgenderism was something pretty common, especially in festivals and in theatre. So taking from that and from the fact that Joker is basicaly everything that exists, character wise we have come to todays joker.

Writers have taken these elements and incorporated them into the Joker.
Grant Morrison treats joker like an entity and batmans polar opposite. He is not only a villain but also an omen of things to come. I see nothing bad about a writer expressing his own take on a character. Also that's not entirely the writer but also the artist has a say in how tha characters is pictured.

Personaly i would be really bored with just the gangster-joker.

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